Allemann, Oliver; Baldridge, Kim K; Siegel, Jay S (2015). Intramolecular C–H insertion vs. Friedel–Crafts coupling induced by silyl cation-promoted C–F activation. Organic Chemistry Frontiers, 2(9):1018-1021.
Silyl cation-promoted aryl C–F activation can lead to formal C–H activation and the formation of new C(ar)–C(alkyl) bonds. Deuterium-labeling experiments suggest an insertion of a phenyl cation into the C–H bond. From competition experiments, a relation between reaction rate and C–H bond strength could be established. Mechanistic parallels are drawn to the Mascarelli reaction.
Silyl cation-promoted aryl C–F activation can lead to formal C–H activation and the formation of new C(ar)–C(alkyl) bonds. Deuterium-labeling experiments suggest an insertion of a phenyl cation into the C–H bond. From competition experiments, a relation between reaction rate and C–H bond strength could be established. Mechanistic parallels are drawn to the Mascarelli reaction.
| Item Type: | Journal Article, refereed, original work |
|---|---|
| Communities & Collections: | 07 Faculty of Science > Department of Chemistry |
| Dewey Decimal Classification: | 540 Chemistry |
| Language: | English |
| Date: | 2015 |
| Deposited On: | 11 Apr 2016 13:16 |
| Last Modified: | 14 Feb 2018 11:26 |
| Publisher: | Royal Society of Chemistry |
| ISSN: | 2052-4110 |
| OA Status: | Hybrid |
| Free access at: | Publisher DOI. An embargo period may apply. |
| Publisher DOI: | https://doi.org/10.1039/C5QO00170F |
Allemann, Oliver